Finding Joy in Entrepreneurship: Expert Insights on Cultivating Happiness and Fulfillment

Happy entrepreneur taking a selfie

As an entrepreneur, it’s easy to get caught up in the busyness of long working hours and a high-pressure environment. There’s a lot to love about being an entrepreneur and having the opportunity to pursue your dreams and work on something that you love, but it’s easy to lose sight of this.

In this article, several entrepreneurs share their tips and insights to help cultivate joy and happiness for a greater enjoyment of the journey.

Separate Your Identity from the Business

You are not your startup. It’s too easy to let your business become your whole identity. I’ve been down that road. The real game changer? Separating the two. Don’t let your identity get so tangled in your company that you can’t see where it ends and you begin. Remember If you are successful, the company might not always be yours. It’s vital to remember: your startup is giant part of your life, not the sum total of it.

Aaron White, Co-Founder and CEO of

Aaron White

Build a Meaningful Relationship with Fear, Uncertainty, and Doubt

What I always tell entrepreneurs is that you will always walk with three friends: fear, uncertainty, and doubt. The path to wellness and happiness as an entrepreneur is building a meaningful relationship with those three. Expect them to always be around and learn to leverage their power rather than fear them.

Tony Fernandes, CEO and CAIO of UserExperience.AI at UEGroup

Tony Fernandes

Enjoy the Process

Many entrepreneurs are so wrapped up in the results and waiting on “When I reach the results I desire, then I’ll be happy.” What I’ve found is that when I enjoy the journey, the process, and the growth achieved on the way to the result, things become so much more fun.

I talk about this a lot in my programs, standing in your personal power, instead of waiting on external circumstances to make you happy. As you are on your way to reaching your goal when we focus on the internal, we show up differently, we attract more clients and customers, and we become a match for the results we desire.

Otherwise, we’re always waiting for the results, waiting on the revenue, waiting on the person to sign up, waiting on the customer to buy the product instead of being our best selves and owning our expertise and who we are.

My best tips to do this are:

  1. Know who you are and the evidence of the results you’ve achieved in the past.
  2. Dig deep into the conviction of why you are so passionate about what you do.
  3. Show up with day one energy, we don’t always get results on day one, but we are so excited to shout what we do from the rooftops.

Crissy Conner, The Visibility Queen

Crissy Conner

Prioritize Joy

Put bluntly, you can focus on all the above, but you won’t feel aligned and successful if you’re not enjoying the journey. The truth is, fun doesn’t distract us from work as was once thought — in fact, it helps get the work done! Research now supports the idea that everyday enjoyment helps us accomplish long-term goals.

If you find yourself pushing back against the idea of having more fun in your business, fearful that dialing up enjoyment runs the risk of being less serious and therefore less successful — then I’d ask you to consider how your beliefs about work ethic, self-worth and productivity might be holding you back from the success you desire?

Your strategy doesn’t have to be either/or. You can work hard and still have fun. You can play and sell. And sometimes, taking a joyful break can be just what you need to reset and find clarity to move forward towards your goals.

Julie Vincent, Mindset & Wellness Coach at Clear Space for Joy

Julie Vincent

Values Exploration and Implementation

As a certified coach, former tech product manager and marketer and current founder, I love sharing tools and tips around cultivating fulfillment while managing stress and burnout for entrepreneurs who are building their businesses and careers.

One simple exercise I do regularly with my clients is “values exploration and implementation.” When people are able to identify the values that mean the most to them, articulate how those values show up in their lives and can put actions in place to prioritize those values, they feel more stable, connected and joyful.

Here’s a simple way to do it on your own or with a partner:

  1. Give yourself about 10 minutes and find a comfortable place to sit where you can think, jot down some thoughts (and speak if you’re with another person)
  2. Think of 3 people that you really admire and would love to emulate – they can be people from work, your personal life or even characters from books or movies. These should be people who make you feel good, confident and happy. Spend about one minute defining your list of people.
  3. Note the characteristics that make these people stand out to you. What about them makes them special when it comes to what they do, how they act, or the way they make you and others feel? Spend about 3 minutes writing down these qualities.
  4. Look through your list of qualities – notice which of them apply to the way you live/are or want to live/be. The attributes and actions that rise to the top are an indication of your values – the things that are most important to you. Spend 2 minutes here.
  5. Choose one attribute or value that really stands out and think about how you incorporate it into your daily life or decisions you make. Would you be more fulfilled or content if you were making decisions based on this value?
  6. Lastly, decide on one change you can make in your life that will put that value top of mind as you work, live and play.

Annette Pearson, Annette Blum Pearson Coaching & Consulting

Annette Pearson

The Hustle Jar

In December of last year I saw reels all over Instagram talking about writing down good things that happen throughout the year and putting those papers into a jar. Then at the end of the year, going through them to relive the highlights of your year.

Well, I have a personal Instagram account to capture the highlights (and travels) of my year in a picturesque fashion. But I saw an opportunity here. I thought:

How can I adapt this to business and have it make an impact daily rather than just at the end of December?

Enter: The Hustle Jar.

At the end of each business day I write down at least ONE good thing that happened at work, plus how it made me feel.

Even on the HARDEST days being an entrepreneur, there is always at least one win that can be marked down. Even if it’s simply “didn’t cry at my desk today.” Noting these since Jan 1 has really helped me end every work day on a *positive* note.

Channing Muller, DCM Communications

Channing Muller

Set Realistic Goals and Celebrate Small Wins

Entrepreneurship can often feel like an uphill journey, with monumental challenges cropping up every day. A useful strategy is to set attainable, realistic goals daily, weekly, or monthly. Reaching these milestones brings satisfaction and a great sense of achievement.

Moreover, celebrating small wins boosts motivation and adds an element of joy, which can help entrepreneurs navigate through stressful times. Every success, no matter how small it may seem, is a step forward—it’s crucial never to undervalue them, as they are the building blocks leading to the overall vision of the business.

Stacey Tapping, CEO & Owner at Beauty Sculpting Room

Stacey Tapping

Don’t Be Outcome-Dependent

As a poker player and entrepreneur, i’ve found the biggest happiness is ‘playing well’ and not being outcome-dependent. Most of the big success stories we hear are based on luck, the 100x case studies we mostly see are right place, right time. But always play the hand you’re dealt to the best of your ability and how could you not be happy?

Tom Leach, Founder of Norsu Media Group

Tom Leach

About the Author

Marc has been building websites and online businesses since 2007. He's built successful businesses in several industries, including web/graphic design, photography, travel, and personal finance. Marc has been featured on Forbes, Business Insider, Flippa, and many others.

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